d100+ Peculiar Pirates

Pirates are sitting on the deck as a figure hiding in a barrel is spying on them

D2 Yar

  1. HAR!
  2. ARRRRR!


D4 Pirate Province

  1. Sea Pirates
  2. Sky Pirate
  3. Space Pirates
  4. Desert Pirates


D6 Pirate Pet (Not ALL Pirates have pets but this one does, fuck you)

  1. Parrot
  2. Monkey
  3. Cat
  4. Rat Terrier
  5. Crocodile
  6. Something…strange 

A blindfolded man stands at the end of a plank extended over the side of a ship

D8 Pirate Parrel

  1. Tricorn Hat
  2. Colorful Bandana
  3. Copious stolen jewelry 
  4. Tall Cavalier boots with big buckles
  5. Big Red Jacket
  6. Ruffled shirt and cuffs
  7. Plentiful Piercings  
  8. Obvious jolly roger stitched somewhere on their clothing

D10 Piratical Prosthetics 

  1. Peg Left Leg
  2. Peg Right Leg
  3. Peg Left and Right Leg
  4. Hook Left Hand
  5. Hook Right Hand
  6. Hook Left and Right Hand
  7. Left Eye patch
  8. Right Eye Patch
  9. Both Eye patches
  10. Roll twice

D10 Pirate Preference (if Space Pirate, just Laser or Graviton or something next to it)

  1. Cutlass
  2. Firearms
    1. Pistol
    2. Musket
    3. Pepperbox
    4. Blunderbuss
    5. 7 Barreled Nock Gun 
    6. Hand Cannon
  3. Boarding ax 
  4. Belaying Pin
  5. Pike
  6. Throwing Knives
  7. Grenades
  8. Cannons
  9. Combo Weapon
    1. Sword-Pistol
    2. Wheelock-Axe
    3. Lantern Shield
    4. Rapier and Parrying Dagger
    5. Gauntlet-Sword
  10. Non-Standard
    1. Man-Catcher
    2. Grappling Hook
    3. Cooper’s Hammer
    4. Oversized Butcher’s Cleaver
    5. Cat O’ Nine Tails 
    6. AN ANCHOR

A man wearing a gray coat, a red sash, and a hat stands on the poop deck of a ship smoking a pipe

D12 Pirate Position

  1. Captain
  2. First Mate
  3. Quartermaster
  4. Navigator
  5. Gunner
  6. Cabin Boy
  7. Boatswain
  8. Surgeon
  9. Cook
  10. Carpenter
  11. Musician
    1. Lute
    2. Drums
    3. Accordion
    4. Violin
    5. Hurdy Gurdy
    6. Flute
  12. Deckhand


D20 Pirate Personality 

  1. Completed obsessed with “Good Form,” even if they occasionally have Bad form
  2. Loveable Rapscallion
  3. Mutinous Backstabbing Bastard
  4. Interested in Loot before all else
  5. Deeply Cynical, they pirate because they can’t do anything else
  6. Disturbingly Optimistic, this is all a game to them, a terrible, wonderful, bloody game
  7. Roaring Drunk All The Time!
  8. Gleefully Malevolent 
  9. Completely certain in their right to do this by Letter of Marque, an excuse for their actions
  10. Extremely superstitious, reads signs from everything, spends much of their time trying to counter bad luck
  11. Always thinks the next ship will be the last haul before a quiet, luxurious retirement.
  12. Fiercely loyal to their comrades-in-arms, even to a fault.
  13. Full of toxic machismo that falters at the slightest resistance
  14. The sort of coward that flings insults from behind but is the first to surrender when things go wrong.
  15. You know that phrase “speak like a sailor”? Well not even sailors speak like this pirate. 
  16. They fear death with an intensity shared only by really old wizards and really wealthy politicians. 
  17. They seem to have absolutely no fear what-so-ever, for good or for ill.
  18. A jaded glutton and hedonist who seeks ever more exotic pleasures.
  19. A goofy, incompotent fool.
  20. One of those rare, legitimately good people who just so happened to fall into a bloodthirsty profession.

A pirate wearing a red sash stands on a beach next to a chest as two men dig a hole in the sand

D100 Pirate Peculiarity aka Fuck Historical Accuracy 

  1. Preposterous Piratical Prosthetics
    1. Working Cannon Arm
    2. Cutlass Legs
    3. Scrying Orb Glass Eye
    4. Peg Legs, Peg Arms, Peg Eyes Too!
    5. Peg Leg made out of a wizard’s staff
    6. Harpoon gun hook-hands
  2. They have spent so much of their life being drunk that their natural movements are similar to those of a trained drunken boxer. Their liver will kill them before anyone else does.
  3. They ate a strange (and disgusting) fruit. Now they have bizarre powers and can’t swim.
  4. They are free from scars, pegs, and hooks and possess both of their eyes. I wonder how long that will last.
  5. Their favorite sea shanty is
    1. Rum Did Me Brother In
    2. The Ballad of Johnny Keelhaul 
    3. Haul Away Home (That we ain’t got)
    4. To The Devil We Go
    5. Fly The Roger (This one is full of dicks jokes)
    6. She’s Got Scurvy, Scabies and Syphilis (But I love her still)
  6. Crew suffers from the inverse ninja law, something fierce. 
  7. Can somehow do that dagger through the sail trick for getting down off the mast.
  8. Climbs like a goddamn monkey through the rigging (in systems where it matters, give them a climb speed)
  9. If beheaded and thrown into the sea, their body will swim thirteen laps around a vessel before sinking. 
  10. Cursed Semi-Immortal Skeleton Pirate!
  11. Knows a variety of minor charms that actually work.
  12. Has their soul signed over to Captain Davy Jones, who will come to collect soon enough
  13. They got a brief viewing of Fiddler’s Green during a hurricane and have made it their life’s goal to reach there again.
  14. Don’t ask how it worked but, one of their parents was human, the other…well the other was…
    1. A SHARK
      1. Goblin
      2. Hammerhead
      3. Great White
      4. Cookie cutter
      5. Megamouth
      6. Sawnose
    2. An Octopus
    3. A Hagfish
    4. A Mola Mola
    5. Lionfish
      1. Angler Fish
      2. Gulper Eel
      3. Blobfish
      4. Vampire Squid
      5. Japanese Spider Crab
      6. Giant Isopod
  15. Has a tattoo for every ship they’ve taken
  16. Can literally pull themselves up by their bootstraps, gravity takes over when their arms get tired
  17. Is 6 inches tall and terribly afraid of the dark
  18. Is a Giant, has to stride across the ocean floor instead of using a boat
  19. Will come back from death if even a drop of their fresh blood meets with sea water
  20. Possesses a Deadman’s Chest, which will only open for whomever kills its last owner
  21. Was a puppeteer prior to becoming a pirate, a few of their old tricks are surprisingly useful in their new career.
  22. Is also a Clown and is prone to slipping on the poop deck 
  23. Is Two Goblins in breeches and a bandana
  24. Their ship is a floating Castle
  25.  Instead of hooks, they have vice grip hands
  26. They possess an especially weird weapon
    1. A Magic Sword
    2. Blood Magic infused Macuahuitl 
    3. Slingshot and magic beans
    4. An alchemical flame-thrower
    5. A mono-atomic edged shattered rum bottle
    6. An actively leaking Wizard’s Staff (random wild magic effects with each bonk)
  27. Got knocked on the head and is now convinced they are a dolphin
  28. Their ship can transform into a giant robot 
  29. They are a coin operated robot! FEED ME DUBLOONS! 
  30. They are a vampire and their Corpse-Ship is manned by a variety of undead
  31. They are a Wizard turned to Piracy to pay off student loans
  32. They are a Sea-Witch seeking the bastard who ate their mermaid wife
  33. Seawater refuses to touch them with an effect similar to intense magnetic repulsion
  34. They are a Were-Kraken 
  35. Their ship is pulled by several dozen Zood 
  36. They had another reason for adventure that inspired them to become a pirate
  37. They are a Cannibal and not afraid to show it.
  38. Their eyepatch is actually a power limiter or something like that
  39. Their back is tattooed with an accurate map of their home waters. They regularly get it updated with sites of interest
  40. Is actually an extra-dimensional being in the shape of a pirate hat that is piloting some poor fool’s body.
  41. They are a crocodile that someone dressed up as a pirate, the rest of the crew don’t seem to notice the difference. 
  42. They are a master of Insult Dueling/Flyting
  43. Knows the True Name of the West Wind, allowing them to call it up on a whim. The other Winds have it out for the pirate though.
  44. They are an out of place modern pirate, armed with modern weaponry and far less romantic ideals
  45. They have an archnemsis Ninja (note to self, Ninja generator?)
  46. Do you wanna know how I got these scars? Carrying a cutlass between my teeth
  47. They are a pirate who doesn’t do anything at all.
  48. Oh shit, they have a submarine!
  49. They are a wacky cyborg powered by Rum (Treasure Planet Long John Silver or One Piece Franky style)
  50. They will swear up and down that they are a privateer, not a pirate. It is all the same to the hangman. 
  51. Has so many strange and extic STDs that they no longer need the S part to transmit them.
  52. Has to drink gunpowder infused rum on a regular basis to “keep away the ghosts”
  53. Made a pact with a demon and must tithe the lion’s share of their loot to it.
  54. They are not a pirate, they are a viking. See? They’ve got a hat with horns on it. Don’t sass me!
  55. They once had a fabulous beard but after putting burning fuses in it to emulate Blackbeard, it caught fire.
  56. Their ship is, instead, a captured and heavily modified Sea-Train
  57. They are in-laws to a Modern Major General 
  58. Their last ship was caught in the Sargasso Sea, they wish to recapture her.
  59. Specifically collects an odd treasure
    1. Prosthetic Hands
    2. Colorful Pearls
    3. Religious relics
    4. Cursed objects
    5. Currency that is no longer minted
    6. Porcelain statuettes 
  60. They carry crude effigies of those who wronged them. The ones whom they’ve taken vengeance upon are headless.
  61. They have captured and buried the loot of 99 ships. One more and they’ll have enough wealth to transform into a Sea-Dragon
  62. They replaced all their teeth with shark’s teeth
  63. This pirate spent so much time in the Crow’s Nest that they turned into a Tengu/Kenku
  64. This Pirate is also Radical Anarchist Catgirl, like Nya~
  65. Has a compass that will lead one to one’s greatest desire, but hell if it won’t be a roundabout journey
  66. They’re a shoot first, ask questions later sort. I don’t know where they learned Necromancy.
  67. They are INCREDIBLY unlucky, every ship they’ve been on has been captured, sunk or run ashore within a week of them boarding it.
  68. They are INCREDIBLY lucky, through almost supernatural circumstances they survive battle and escape capture. 
  69. They’ve got three peg legs.
  70. Prefers conducting land and river raids to the open sea.
  71. They (and their crew) are dressed entirely out of the Spirit Halloween’s Sexy Pirate section
  72. The New World has changed them in strange and terrible ways 
  73. They owe significant sums to the Crab Alliance, if they can’t pay it back their skeleton will be forced to pay it off under the waves.
  74. They’ve been to the Fountain of Youth and gained a good 200 years. But hard living (and interaction with Iron) has sapped away their youth and time is catching up.
  75. They are a seafaring Mushman 
  76. To avoid scurvy, they’ve taken up bonsai lime horticulture
  77. They have tasted the flesh of the Leviathan and can never die of drowning. The act of drowning is still terribly painful. 
  78. Was cursed to be unable to ever step foot on dry land again.
  79. Is being pursued by
    1. Bears
    2. The Admiralty
    4. A Rival Pirate 
    5. The ghosts of all they’ve ever killed
    6. A clockwork crocodile
  80. They honestly have no idea how to sail a ship or fight, they’ve gotten to this point entirely by rodomontade and luck
  81. They’re stitched together out of 1d6+1 pirates.
  82. They were raised by Pirates but upon their 21st birthday they have sworn to defect and hunt down all Pirates
  83. They were once a legit noble but have fallen on hard times and had to resort to piracy
  84. They were once Cottagecore, but they were tired of being nice and just wanted to go ape shit. 
  85. They have dreams of being a great chef and exalt in pillaging spices.
  86. Is part of a Pirate Fleet of 3d6 ships
  87. Is the nemesis of an eternally youthful fairy prince, who might actually be the crueler of the two
  88. They can summon a variety of sea creatures for short periods of time.
    1. Many Crabs
    2. Sea Otters
    3. Mr. Dolphin
    4. Sharks!
    5. Swarms of Jellyfish
  89. Their enchanted Earrings make it impossible for them to fall overboard, they have to take them out to even get off the ship.
  90. One of their eyes can extend out into a spyglass
  91. They ride upon a high rise with their crew of angry Accountant-Pirates, The CRIMSON PERMANENT ASSURANCE 
  92. They can tie every knot known to mankind, and some that defy logic such as the Double Gnordian. 
  93. They are unable to resist taking on dares and is a hopeless gambler
  94. They somehow got their greedy hands on a $%^&ing Magic Item!
  95. A bulging eyed madman from the future appeared before them one day and gave them a blood powered Named Chainsaw. Woe and Fear to all those who meet them.
  96. They have a twin who is in the Navy. They sometimes switch places for shits and giggles.
  97. They are actually working for an Eccentric Fantasy Millionaire.
  98. They were once a figurehead on the front of a ship, but a passing fairy brought them to life for a lark.
  99. They have absolutely shit taste in music and are immune to the calls of mermaids and sirens.
  100. They’re the Pirate King, don’t question it. 
Liked it? Take a second to support TheLawfulNeutral on Patreon!
Become a patron at Patreon!

Leave a Reply

Your email address will not be published. Required fields are marked *

This site uses Akismet to reduce spam. Learn how your comment data is processed.